9-iodo-3,3-bis(methoxycarbonyl)bicyclo[4.3.0]non-1(9)-en-8-one | 498555-99-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 9-iodo-3,3-bis(methoxycarbonyl)bicyclo[4.3.0]non-1(9)-en-8-one
• 英文别名: dimethyl 3-iodo-2-oxo-4,6,7,7a-tetrahydro-1H-indene-5,5-dicarboxylate
• CAS: 498555-99-0
• 化学式: C₁₃H₁₅IO₅
• 分子量: 378.164
• InChiKey: DOUCLAGNSLNVQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-iodo-3,3-bis(methoxycarbonyl)bicyclo[4.3.0]non-1(9)-en-8-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以87%的产率得到3,3-bis(methoxycarbonyl)bicyclo[4.3.0]non-1(9)-en-8-one
  参考文献：
  名称：

  New entry to the Pauson–Khand reaction: trimethylgermyl group at the triple bond terminus as a latent functional group

  摘要：

  The Pauson-Khand reaction of enynes possessing a trimethylgermyl group at the alkyne terminus afforded the corresponding bicyclo[3.3.0]octenone and bicyclo[4.3.0]nonenone skeletons in a stereoselective manner. The resulting trimethylgermyl group of the bicyclic compounds was then converted to the iodo group, which was used for further elaboration. Thus, the trimethylgermyl group at the triple bond terminus was shown to be a precursor for other appendages. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.041
• 作为产物：
  描述：

  3,3-bis(methoxycarbonyl)-9-(trimethylgermyl)bicyclo[4.3.0]non-1(9)-en-8-one 在 N-碘代丁二酰亚胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 36.0h， 以92%的产率得到9-iodo-3,3-bis(methoxycarbonyl)bicyclo[4.3.0]non-1(9)-en-8-one
  参考文献：
  名称：

  New entry to the Pauson–Khand reaction: trimethylgermyl group at the triple bond terminus as a latent functional group

  摘要：

  The Pauson-Khand reaction of enynes possessing a trimethylgermyl group at the alkyne terminus afforded the corresponding bicyclo[3.3.0]octenone and bicyclo[4.3.0]nonenone skeletons in a stereoselective manner. The resulting trimethylgermyl group of the bicyclic compounds was then converted to the iodo group, which was used for further elaboration. Thus, the trimethylgermyl group at the triple bond terminus was shown to be a precursor for other appendages. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.041

文献信息

• Trimethylgermyl group in Pauson–Khand reaction
  作者：Chisato Mukai、Takashi Kozaka、Yukihiro Suzuki、In Jong Kim

  DOI：10.1016/s0040-4039(02)02056-7

  日期：2002.11

  The Pauson–Khand reaction of enynes possessing the trimethylgermyl group at the alkyne terminus stereoselectively afforded the corresponding bicyclo[3.3.0]octenone and bicyclo[4.3.0]decenone skeletons. The formed trimethylgermyl group of the bicyclic compound was then converted to the iodo group, which was used for further elaboration. Thus the trimethylgermyl group at the triple bond terminus was

  炔烃末端具有三甲基锗烷基的烯炔的Pauson-Khand反应立体选择性地提供了相应的双环[3.3.0]辛烯酮和双环[4.3.0]癸烯酮骨架。然后将形成的双环化合物的三甲基锗烷基转化为碘基，用于进一步加工。因此，显示出在三键末端的三甲基锗烷基成为其他附属物的前体。